Arctigenin: a lignan from Arctium lappa

Haiyan Gao; Guanglei Li; Junhe Zhang; Jie Zeng

doi:10.1107/S1600536808021752

. 2008 Jul 19;64(Pt 8):o1538. doi: 10.1107/S1600536808021752

Arctigenin: a lignan from Arctium lappa

Haiyan Gao ^a, Guanglei Li ^a, Junhe Zhang ^a, Jie Zeng ^a,^*

PMCID: PMC2962163 PMID: 21203243

Abstract

The title compound {systematic name: (3R-trans)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4,5-dihydrofuran-2(3H)-one}, C₂₁H₂₄O₆, has a dibenzylbutyrolactone skeleton. The two aromatic rings are inclined at a dihedral angle of 68.75 (7)° with respect to each other. The lactone ring adopts an envelope conformation. A series of O—H⋯O and C—H⋯O hydrogen bonds contribute to the stabilization of the crystal packing. The absolute configuration was assigned on the basis of the published literature.

Related literature

For related literature, see: Awale et al. (2006 ▶). For a similar structure, see: Bruno-Colmenárez et al. (2007 ▶).

Experimental

Crystal data

C₂₁H₂₄O₆
M _r = 372.40
Orthorhombic,
a = 9.4845 (19) Å
b = 10.065 (2) Å
c = 19.915 (4) Å
V = 1901.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 (2) K
0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.987, T _max = 0.991
13910 measured reflections
2581 independent reflections
2449 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.079
S = 1.06
2581 reflections
251 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021752/bt2739sup1.cif

e-64-o1538-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021752/bt2739Isup2.hkl

e-64-o1538-Isup2.hkl^{(126.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2ⁱ	0.90 (2)	2.04 (2)	2.8280 (17)	146 (2)
O5—H5⋯O6	0.90 (2)	2.22 (2)	2.6799 (18)	111.7 (17)
O5—H5⋯O1ⁱ	0.90 (2)	2.58 (2)	3.2406 (18)	130.8 (16)
C3—H3⋯O5ⁱⁱ	0.95	2.34	3.278 (2)	168
C14—H14A⋯O4ⁱⁱⁱ	0.99	2.86	3.687 (2)	142
C14—H14B⋯O5^iv	0.99	2.42	3.373 (2)	162
C20—H20⋯O4ⁱⁱⁱ	0.95	2.53	3.446 (2)	162

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

supplementary crystallographic information

Comment

Arctigenin has been identified as an antitumor agent with the ability to eliminate the tolerance of cancer cells to nutrient strarvation (Awale et al., 2006).

The title compound has a dibenzylbutyrolactone skeleton (Fig. 1). The two aromatic rings have a dihedral angle of 68.75 (7)°. The lactone ring adopts an envelope conformation. A series of O—H···O and C—H···O hydrogen bonds contribute to the stabilization of the crystal packing (Table 1).

Experimental

Arctigenin was isolated from Chinese medicine Arctium lappa. Crystal blocks were obtained by natural evaporation of a methanolic solution.